WO2012054097A8 - Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt - Google Patents

Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt Download PDF

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Publication number
WO2012054097A8
WO2012054097A8 PCT/US2011/030252 US2011030252W WO2012054097A8 WO 2012054097 A8 WO2012054097 A8 WO 2012054097A8 US 2011030252 W US2011030252 W US 2011030252W WO 2012054097 A8 WO2012054097 A8 WO 2012054097A8
Authority
WO
WIPO (PCT)
Prior art keywords
mono
lithium salt
sulfate
sulfoisophthalic acid
acetic acid
Prior art date
Application number
PCT/US2011/030252
Other languages
French (fr)
Other versions
WO2012054097A1 (en
Inventor
Timothy A. Oster
Michael Todd Coleman
Original Assignee
Future Fuel Chemical Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from PCT/US2010/053186 external-priority patent/WO2011049940A2/en
Application filed by Future Fuel Chemical Company filed Critical Future Fuel Chemical Company
Priority to CA2815049A priority Critical patent/CA2815049A1/en
Priority to JP2013534897A priority patent/JP5760089B2/en
Priority to MX2013004254A priority patent/MX2013004254A/en
Priority to EP11834767.3A priority patent/EP2630119A4/en
Priority to US13/880,602 priority patent/US8884045B2/en
Publication of WO2012054097A1 publication Critical patent/WO2012054097A1/en
Publication of WO2012054097A8 publication Critical patent/WO2012054097A8/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification

Abstract

There is disclosed a process for making a mono-lithium salt of 5-sulfoisophthalic acid (LiSIPA) having less than 500 ppm sulfate. The process uses a reaction mixture of water, a lithium cation producing compound, and 5-sulfoisophthalic acid. The reaction mixture is heated to reflux, cooled, filtered and washed with acetic acid to obtain a high quality LiSIPA having less than 500 ppm sulfate. Also disclosed is a high quality, non-purified reaction product containing a mono-lithium salt of 5-sulfoisophthalic acid and having less than 500 ppm sulfate.
PCT/US2011/030252 2010-10-19 2011-03-29 Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt WO2012054097A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA2815049A CA2815049A1 (en) 2010-10-19 2011-03-29 Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt
JP2013534897A JP5760089B2 (en) 2010-10-19 2011-03-29 Preparation of 5-sulfoisophthalic acid monolithium salt with low sulfuric acid ester concentration using acetic acid washing
MX2013004254A MX2013004254A (en) 2010-10-19 2011-03-29 Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt.
EP11834767.3A EP2630119A4 (en) 2010-10-19 2011-03-29 Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt
US13/880,602 US8884045B2 (en) 2010-10-19 2011-03-29 Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
USPCT/US2010/0053186 2010-10-19
USPCT/US2010/005318 2010-10-19
PCT/US2010/053186 WO2011049940A2 (en) 2009-10-20 2010-10-19 Use of an acetic acid/water solvent mixture for the preparation of low-sulfate 5-sulfoisophthalic acid, mono-lithium salt from 5-sulfoisophthalic acid

Publications (2)

Publication Number Publication Date
WO2012054097A1 WO2012054097A1 (en) 2012-04-26
WO2012054097A8 true WO2012054097A8 (en) 2013-05-30

Family

ID=45975545

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/030252 WO2012054097A1 (en) 2010-10-19 2011-03-29 Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt

Country Status (5)

Country Link
EP (1) EP2630119A4 (en)
JP (1) JP5760089B2 (en)
CA (1) CA2815049A1 (en)
MX (1) MX2013004254A (en)
WO (1) WO2012054097A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9359292B2 (en) 2009-10-20 2016-06-07 Futurefuel Chemical Company Use of an acetic acid/water solvent mixture for the preparation of low-sulfate 5-sulfoisophthalic acid, mono-lithium salt from 5-sulfoisophthalic acid
JP2014508163A (en) 2011-03-02 2014-04-03 フューチャーフューエル ケミカル カンパニー Metal salt of dialkyl ester of 5-sulfoisophthalic acid and preparation method thereof
US8809565B2 (en) 2011-08-29 2014-08-19 Futurefuel Chemical Company 5-sulfoisophthalic acid salts and process for the preparation thereof
CN102993063A (en) * 2012-07-30 2013-03-27 枣庄市泰瑞精细化工有限公司 Preparation method of isophthalic acid-5-sodium sulfonate

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5013252B2 (en) * 1972-07-21 1975-05-19
US6433107B1 (en) * 1995-08-31 2002-08-13 Prisma Fibers, Inc. Fiber-forming polyamide with concentrate of polyamide and sulfonated aromatic acid
US6537475B1 (en) * 1995-08-31 2003-03-25 Prisma Fibers, Inc. Melt extrusion spinning polyamide fibers with sulfonated reagent
USH1760H (en) * 1997-01-08 1998-11-03 Hoechst Celanese Corporation Process for glycol esters of an alkali metal salt of 5-sulfoisophthalic acid
US6479619B1 (en) * 2001-03-15 2002-11-12 E. I. Du Pont De Nemours And Company Sulfoisophthalic acid solution process therewith
JP2007063714A (en) * 2005-08-31 2007-03-15 Toray Ind Inc Ultrafine polyester fiber and cloth
US8465818B2 (en) * 2005-10-07 2013-06-18 M & G Usa Corporation Polyamides and polyesters blended with a lithium salt interfacial tension reducing agent
CN101279940B (en) * 2008-05-20 2012-06-06 北京金方博源科技发展有限公司 Preparation of isophthalic acid-5-sulfonic acid, ester, salt and ester salt thereof
US9359292B2 (en) * 2009-10-20 2016-06-07 Futurefuel Chemical Company Use of an acetic acid/water solvent mixture for the preparation of low-sulfate 5-sulfoisophthalic acid, mono-lithium salt from 5-sulfoisophthalic acid

Also Published As

Publication number Publication date
EP2630119A4 (en) 2014-04-23
JP2014502956A (en) 2014-02-06
CA2815049A1 (en) 2012-04-26
EP2630119A1 (en) 2013-08-28
MX2013004254A (en) 2013-06-03
JP5760089B2 (en) 2015-08-05
WO2012054097A1 (en) 2012-04-26

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